Heteroditopic Rebek's imide directs the reactivity of homoditopic olefins within desolvated quaternary assemblies in the solid state

Angewandte Chemie - International Edition

Volumn 45, Issue 4, 2006, Pages 646-650

  Varshney, Dushyant B ^a   Gao, Xiuchun ^a   Friščić, Tomislav ^a   MacGillivray, Leonard R ^a  

^a E11 SSH   (United States)

Author keywords

Cycloaddition; Receptors; Self assembly; Solid state reactions; Topochemistry

Indexed keywords

COMPLEXATION; DIMERIZATION; HYDROGEN BONDS; SELF ASSEMBLY; SINGLE CRYSTALS;

CYCLOADDITION; RECEPTORS; SOLID-STATE REACTIONS; TOPOCHEMISTRY;

OLEFINS;

EID: 31044449831     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502294     Document Type: Article

References (62)

1. a) J.-M Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995;
2. b) J. W. Steed, J. L. Atwood, Supramolecular Chemistry, Wiley, Chichester, 2000.
3. a) P. A. Gale, Coord. Chem. Rev. 2003, 240, 191;
4. b) P. D. Beer, P. A. Gale, Angew. Chem. 2001, 113, 502;
5. Angew. Chem. Int. Ed. 2001, 40, 486;
6. c) G. Tumcharern, T. Tuntulani, S. J. Coles, M. B. Hursthouse, J. D. Kilburn, Org. Lett. 2003, 5, 4971.
7. a) J. L. Sessler, J. Jayawickramarajah, Chem. Commun. 2005, 1939;
8. b) S. Sivakova, S. J. Rowan, Chem. Soc. Rev. 2005, 34, 9.
9. D. H. Lee, J. R. Granja, J. A. Martinez, K. Severin, M. R. Ghadri, Nature 1996, 382, 525.
10. a) J. M. Mahoney, J. P. Davis, A. M. Beatty, B. D. Smith, J. Org. Chem. 2003, 68, 9819;
11. b) J. M. Mahoney, A. M. Beatty, B. D. Smith, J. Am. Chem. Soc. 2001, 123, 5847.
12. C. J. Baylies, L. P. Harding, J. C. Jeffrey, T. Riis-Johannessen, C. R. Rice, Angew. Chem. 2004, 116, 4615;
13. Angew. Chem. Int. Ed. 2004, 43, 4515.
14. F. Diederich, P. J. Stang in Templated Organic Synthesis, Wiley-VCH, Weinheim, 2000.
15. M. C. T. Fyfe, J. F. Stoddart, Acc. Chem. Res. 1997, 30, 393.
16. T. R. Kelly, G. J. Bridger, C. Zhao, J. Am. Chem. Soc. 1990, 112, 8024.
17. a) D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242;
18. Angew. Chem. Int. Ed. Engl. 1996, 35, 1155;
19. b) S. J. Rowan, S. J. Cantrill, G. R. L. Cousins, J. K. M. Sanders, J. F. Stoddart, Angew. Chem. 2002, 114, 1528;
20. Angew. Chem. Int. Ed. 2002, 41, 898 - 952;
21. c) J. S. Lindsey, New J. Chem. 1991, 15, 153.
22. a) J. Rebek, Jr., Angew. Chem. 1990, 102, 261;
23. Angew. Chem. Int. Ed. Engl 1990, 29, 245;
24. b) J. Rebek, Jr., Acc. Chem. Res. 1990, 23, 399.
25. G. M. J. Schmidt, Pure Appl. Chem. 1971, 43, 647.
26. a) V. Enkelmann, G. Wegner, K. Novak, K. B. Wagener, J. Am. Chem. Soc. 1993, 115, 10 390;
27. b) T. Friščić, L. R. MacGillivray, Z. Kristallogr. 2005, 220, 351.
28. S. White, E. E. Baird, P. B. Dervan, Biochemistry 1996, 35, 12 532.
29. For a discussion on solvent incorporation in solid-state reactions, see: "Photochemical Solid-to-Solid Reactions": A. E. Keating, M. A. Garcia-Garibay in Molecular and Supramolecular Photochemistry, Vol. 2 (Eds.: V. Ramamurthy, K. Schanze), Marcel Dekker, New York, 1998.
30. a) L. R. Nassimbeni, Acc. Chem. Res. 2003, 36, 631;
31. b) J. L. Atwood, L. J. Barbour, A. Jerga, B. L. Schottel, Science 2002, 298, 1000.
32. D. Braga, F. Grepioni, Angew. Chem. 2004, 116, 4092;
33. Angew. Chem. Int. Ed. 2004, 43, 4002.
34. For recent studies to direct the [2+2] photodimerization in the solid state using organic molecules, see: a) A. Natarajan, J. T. Mague, K. Venkatesan, V. Ramamurthy, Org. Lett. 2005, 7, 1895;
35. b) S. Hirano, S. Toyota, F. Toda, Chem. Commun. 2005, 634;
36. c) T. Caronna, R. Liantonio, T. A. Logothetis, P. Metrangolo, T. Pilati, G. Resnati, J. Am. Chem. Soc. 2004, 126, 4500;
37. d) X. Gao, T. Friščić, L. R. MacGillivray, Angew. Chem. 2003, 115, 234;
38. Angew. Chem. Int. Ed. 2004, 43, 232;
39. e) N. Shan, W. Jones, Tetrahedron Lett. 2003, 44, 3687;
40. f) D. G. Amirakis, M. A. Garcia-Garibay, S. J. Rowan, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2001, 113, 4386;
41. Angew. Chem. Int. Ed. 2001, 40, 4256;
42. g) L. R. MacGillivray, J. L. Reid, J. A. Ripmeester, J. Am. Chem. Soc. 2000, 122, 7817;
43. h) Y. Ito, B. Borecka, J. Trotter, J. R. Scheffer, Tetrahedron Lett. 1995, 36, 6083.
44. For recent studies to direct the [2+2] photodimerization in the solid state using metalions, see: a) Q. Chu, D. C. Swenson, L. R. MacGillivray, Angew. Chem. 2005, 117, 3635;
45. Angew. Chem. Int. Ed. 2005, 44, 3569;
46. b) N. L. Toh, M. Nagarathinam, J. J. Vittal, Angew. Chem. 2005, 117, 2277;
47. Angew. Chem. Int. Ed. 2005, 44, 2237;
48. c) G. S. Papaefstathiou, Z. Zhong, L. Geng, L. R. MacGillivray, J. Am. Chem. Soc. 2004, 126, 9158.
49. a) R. Faraoni, R. K. Castellano, V. Gramlich, F. Diederich, Chem. Commun. 2004, 370;
50. b) R. K. Castellano, V. Gramlich, F. Diederich, Chem. Eur. J. 2002, 8, 118;
51. c) R. A. Pascal, Jr., D. M. Ho, J. Am. Chem. Soc. 1993, 115, 8507.
52. a) T. Bach, H. Bergmann, K. Harms, Org. Lett. 2001, 3, 601;
53. b) K. Mori, O. Murai, S. Hashimoto, Y. Nakamura, Tetrahedron Lett. 1996, 37, 8523.
54. These conditions can be considered harsh for an organic solid (see Ref. [16a]).
55. -1 (see: a) R. A. Nyquist, S. L. Fiedler, Vib. Spectrosc. 1995, 8, 365;
56. b) R. Langner, G. Zundel, J. Chem. Soc. Faraday Trans. 1995, 91, 3831).
57. Y. Guo, S. R. Byrn, G. J. Zografi, Pharm. Pharmacol. Commun. 2000, 89, 128.
58. For a symmetrical molecule that organizes two different substrates, see: T. R. Kelly, C. Zhao, G. J. Bridger, J. Am. Chem. Soc. 1989, 111, 3744.
59. B. Moulton, M. J. Zaworotko, Chem. Rev. 2001, 101, 1629.
60. The antiparallel orientation is consistent with the tendency of organic molecules to form centrosymmetric solids, see: G. R. Desiraju in Crystal Engineering: The Design of Organic Solids, Elsevier, Amsterdam, 1989.
61. '[28] J. G. Stack, D. P. Curran, S. V. Geib, J. Rebek, Jr., P. Ballester, J. Am. Chem. Soc. 1992, 114, 7007.
62. G. M. Sheldrick, SHELXL-97, Program for Refinement of Crystal Structure, University of Göttingen, Göttingen, Germany, 1997.